2-N,5'-O,3'-O-triisobutyryl-8-chloro-2'-deoxyguanosine | 865873-76-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 2-N,5'-O,3'-O-triisobutyryl-8-chloro-2'-deoxyguanosine
• CAS: 865873-76-3
• 化学式: C₂₂H₃₀ClN₅O₇
• 分子量: 511.962
• InChiKey: FMVUXVZJHJCKKA-BFHYXJOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.42
• 重原子数：
  35.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  154.5
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  2-N,5'-O,3'-O-triisobutyryl-8-chloro-2'-deoxyguanosine 在 N-甲基咪唑 、 4-二甲氨基吡啶 、 sodium methylate 、 N,N-二异丙基乙胺 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 为溶剂， 反应 2.75h， 生成 2-N-isobutyryl-5'-O-dimethoxytrityl-8-chloro-2'-deoxyguanosin-3'-yl β-cyanoethyl-N,N-diisopropylphosphoramidite
  参考文献：
  名称：

  Base Pair Stability of 8-Chloro- and 8-Iodo-2‘-deoxyguanosine Opposite 2‘-Deoxycytidine:  Implications Regarding the Bioactivity of 8-Oxo-2‘-deoxyguanosine

  摘要：

  8-Oxo-2'-deoxyguanosine (OdG) is an abundant and promutagenic damaged nucleotide that has been linked to aging and disease. To gain insight into the alternate base pairings of OdG, 8-chloro- and 8-iodo-2'-deoxyguanosine were incorporated into oligonucleotides and, along with 2'-deoxyguanosine and 8-bromo-2'-deoxyguanosine, were tested for their stability in base pairs opposite dC. We found a strong correlation between increased atomic radius and bond length at C8 and decreased base pair stability. These findings along with NMR studies on the base conformation of the corresponding nucleosides support the theory that the steric bulk of the 8-oxygen plays a role in OdG mutation and disease.

  DOI：

  10.1021/ja052578k
• 作为产物：
  描述：

  N²,3',5'-triisobutyryl-2'-deoxyguanosine 在 N-chloro-succinamide 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以41%的产率得到2-N,5'-O,3'-O-triisobutyryl-8-chloro-2'-deoxyguanosine
  参考文献：
  名称：

  Base Pair Stability of 8-Chloro- and 8-Iodo-2‘-deoxyguanosine Opposite 2‘-Deoxycytidine:  Implications Regarding the Bioactivity of 8-Oxo-2‘-deoxyguanosine

  摘要：

  8-Oxo-2'-deoxyguanosine (OdG) is an abundant and promutagenic damaged nucleotide that has been linked to aging and disease. To gain insight into the alternate base pairings of OdG, 8-chloro- and 8-iodo-2'-deoxyguanosine were incorporated into oligonucleotides and, along with 2'-deoxyguanosine and 8-bromo-2'-deoxyguanosine, were tested for their stability in base pairs opposite dC. We found a strong correlation between increased atomic radius and bond length at C8 and decreased base pair stability. These findings along with NMR studies on the base conformation of the corresponding nucleosides support the theory that the steric bulk of the 8-oxygen plays a role in OdG mutation and disease.

  DOI：

  10.1021/ja052578k